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Carbutamide

Carbutamide structure

Carbutamide 

structure
  • CAS No:

    339-43-5

  • Formula:

    C11H17N3O3S

  • Chemical Name:

    Carbutamide

  • Synonyms:

    Benzenesulfonamide,4-amino-N-[(butylamino)carbonyl]-;Urea,1-butyl-3-sulfanilyl-;Sulfanilamide,N1-(butylcarbamoyl)-;4-Amino-N-[(butylamino)carbonyl]benzenesulfonamide;BZ 55;U 6987;Alentin;N-(4-Aminobenzenesulfonyl)-N′-butylurea;Aminophenurobutane;Bucarban;Bucrol;Burcol;N′-(Butylcarbamoyl)sulfanilamide;N-Butyl-N′-sulfanilylurea;1-Butyl-3-sulfanilylurea;Carbutamide;Emedan;Glucidoral;Glybutamide;Invenol;Nadisan;Norboral;Oranil;Orasulin;Diaboral;Oranyl;N′-(4-Aminobenzenesulfonyl)-N-butylurea;N′-(4-Aminophenylsulfonyl)-N-butylurea;N′-(4-Aminophenylsulfonyl)-N-n-butylurea;Carbutamid;N-Sulfanilyl-N′-butylurea;Bukarban;Nadizan;Butisulfina;Inbuton;Glucofren;NSC 242409;NSC 246862;1-(4-Aminophenyl)sulfonyl-3-butylurea;1331317-37-3

  • Categories:

    Active Pharmaceutical Ingredients  >  Hormones and the Endocrine System

Description

Carbutamide (BZ-55) is an orally active and first-generation sulfonylurea with hypoglycemic activity[1].


Carbutamide is a sulfonamide and a member of benzenes.|Carbutamide is a first-generation sulfonylurea with hypoglycemic activity. Carbutamide was one of the first sulfonylurea compounds used but was withdrawn from the market due to toxic effects on bone marrow. This agent has a long half-life.|A sulfonylurea antidiabetic agent with similar actions and uses to CHLORPROPAMIDE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p277)

Carbutamide Basic Attributes

271.335

271.34

206-424-4

E3K8P4869P

246862|242409

DTXSID8022741

C83597

Crystals

A - Alimentary tract and metabolism

2935009090

Characteristics

110

1.01

1.266g/cm3

144-145 °C

1.564

In water, 535 mg/l @ 37 deg C

Oral-rat LD50: 4400 mg/kg; Oral-Mouse LD50: 250 mg/kg

Thermal decomposition emits toxic nitrogen oxides and sulfur oxide fumes

Safety Information

Treasury is ventilated, low temperature and dry; stored separately from food materials

P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

H315

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

Toxicity

highly toxic

...SODIUM CARBONATE REDUCED...DRUG'S TERATOGENIC & LETHAL ACTION IN RAT.|DRUGS THAT MAY INCR RISK OF HYPOGLYCEMIA FROM SULFONYLUREAS INCL OTHER HYPOGLYCEMIC AGENTS, SULFONAMIDES, PROPRANOLOL, SALICYLATES, CLOFIBRATE, PHENYLBUTAZONE, PROBENECID, DICUMAROL, CHLORAMPHENICOL, MONOAMINE OXIDASE INHIBITORS, & ALCOHOL. /SULFONYLUREAS/|ALCOHOL & SALICYLATES BECAUSE OF THEIR DIRECT HYPOGLYCEMIC ACTION, MAY PRECIPITATE HYPOGLYCEMIC COMA IN PT RECEIVING SULFONYLUREAS. ... PROPRANOLOL, BY INTERFERING WITH GLYCOGENOLYSIS & GLUCAGON RELEASE, ENHANCES THE HYPOGLYCEMIC ACTION OF SULFONYLUREAS. /SULFONYLUREAS/|THE SULFONYLUREA-MEDIATED SECRETION OF INSULIN CAN BE MODIFIED BY CONCOMITANT PERFUSION OF SECOND DRUG THAT DISPLACES SULFONYLUREA IN PANCREAS. THUS, THE DRUG INTERACTION AT THE TARGET ORGAN OR RECEPTOR SITE SHOULD BE UNDERSTOOD TO PROVIDE ADEQUATE DRUG THERAPY.|For more Interactions (Complete) data for 1-BUTYL-3-SULFANILYLUREA (8 total), please visit the HSDB record page.

Drug Information

Hypoglycemic Agents|MEDICATION (VET): CARBUTAMIDE HAD A SIGNIFICANT ANTITHYROID EFFECT IN RATS WHEN ADDED TO THEIR DIETS FOR 10-14 DAYS. IT REDUCED THYROID (131)-IODINE UPTAKE & REDUCED SYNTHESIS OF THYROXINE.|CARBUTAMIDE.../IS/ A SULFANILAMIDE ORAL HYPOGLYCEMIC DRUG USED IN DIABETES...|THE SULFONYLUREAS SHOULD BE USED ONLY IN PATIENTS WITH DIABETES OF THE INSULIN-INDEPENDENT TYPE WHO CANNOT BE TREATED WITH DIET ALONE. /SULFONYLUREAS/|HYPOGLYCEMIC AGENT

HEMATOLOGICAL (LEUKOPENIA, AGRANULOCYTOSIS, THROMBOCYTOPENIA, PANCYTOPENIA, & HEMOLYTIC ANEMIA), CUTANEOUS (RASHES, PHOTOSENSITIVITY), GI (NAUSEA, VOMITING, RARELY HEMORRHAGE), & HEPATIC (INCR SERUM ALKALINE PHOSPHATASE, CHOLESTATIC JAUNDICE) REACTIONS HAVE BEEN REPORTED. /SULFAMYLUREA/|THE INCREASE IN CARDIOVASCULAR MORTALITY DURING TREATMENT WITH SULFONYLUREAS...IS THE MAJOR TOXIC EFFECT SO FAR REPORTED. /SULFONYLUREAS/|SULFONYLUREAS SHOULD NOT BE USED IN PATIENTS WITH HEPATIC OR RENAL INSUFFICIENCY BECAUSE OF THE IMPORTANT ROLE OF THE LIVER IN THEIR METABOLISM & OF KIDNEY IN EXCRETION OF THE DRUGS & THEIR METABOLITES. INTOLERANCE TO ALCOHOL...OCCURS OCCASIONALLY IN PT TAKING SULFONYLUREAS. /SULFONYLUREAS/|THESE AGENTS ARE...NOT RECOMMENDED FOR USE IN PREGNANCY... TERATOGENESIS IN ANIMALS HAS BEEN OBSERVED TO FOLLOW THE ADMIN OF LARGE DOSES. /SULFONYLUREAS/|For more Drug Warnings (Complete) data for 1-BUTYL-3-SULFANILYLUREA (7 total), please visit the HSDB record page.

Substances which lower blood glucose levels. (See all compounds classified as Hypoglycemic Agents.)

THE SULFONYLUREAS ARE READILY ABSORBED FROM THE GI TRACT. THE MOST IMPORTANT DIFFERENCE AMONG THE SULFONYLUREAS, FOR CLINICAL PURPOSE, IS IN THEIR DURATION OF ACTION... /SULFONYLUREAS/_|SULFONYLUREAS ARE LARGELY BOUND TO PLASMA PROTEINS & ARE DISTRIBUTED IN THE EXTRACELLULAR SPACE. /SULFONYLUREAS/

...IN MAN APPROX ONE-THIRD OF THE EXCRETED DOSE IS REPRESENTED BY THE N-ACETYLATED METABOLITE. LARGE SPECIES VARIATIONS HAVE BEEN DETECTED; THE RABBIT PRODUCES SIGNIFICANT AMT...WHILE MONKEY & DOGS ARE LOW OR VERY LOW ACETYLATORS & MAN OCCUPIES AN INTERMEDIATE POSITION.|THEY ARE HYDROXYLATED IN THE LIVER TO ACTIVE & INACTIVE PRODUCTS WHICH ARE ALMOST TOTALLY EXCRETED IN THE URINE. /SULFONYLUREAS/

SULFONYLUREAS STIMULATE ISLET TISSUE TO SECRETE INSULIN. ... SULFONYLUREAS CAUSE DEGRANULATION OF THE BETA CELLS, A PHENOMENON ASSOCIATED WITH INCR RATE OF SECRETION OF INSULIN. ...THEY ARE EFFECTIVE IN INSULIN-INDEPENDENT DIABETIC PATIENTS IN WHOM THE PANCREAS RETAINS THE CAPACITY TO SECRETE INSULIN. /SULFONYLUREAS/

FOURTEEN PT TREATED WITH CARBUTAMIDE HAD TRANSIENT HEMIPARESIS. 4 HAD IRREVERSIBLE NEUROLOGIC DEFECTS, & 5 EXPIRED AFTER HYPOGLYCEMIC COMA. NEARLY 70 OF THE EPISODES OCCURRED WITHIN THE FIRST 15 DAYS OF THE SULFONYLUREA TREATMENT.

Aminophenurobutane

Carbutamide Use and Manufacturing

Methods of Manufacturing

...from butylurea and sulfanilamide: Samaniego, Spanish patent 229,696 (1956), CA 51, 7413 (1957); Haack, Hagedorn, US patent 2,907,692 (1959 to Boehringer, Mann). Alternate route: Haack, Hagedorn, US patent 2,997,375 (1961 to Boehringer, Mann).|REACTION OF BUTYLUREA WITH SULFANILAMIDE

Uses

Antidiabetic.

Production

(1979) NOT PRODUCED COMMERCIALLY IN U.S.|(1981) NOT PRODUCED COMMERCIALLY IN U.S.

Benzenesulfonamide, 4-amino-N-[(butylamino)carbonyl]-: INACTIVE

PHARMACEUTICAL COMPOUNDS TO BE DETERMINED ARE OXIDIZED BY CERIUM(IV). THE CONCENTRATION OF CE(III) FORMED IS MEASURED SPECTROFLUORIMETRICALLY.

A HIGH PRESSURE LIQUID CHROMATOGRAPHIC METHOD IS DESCRIBED FOR DETERMINING GLIBENCLAMIDE IN SERUM. THIS METHOD IS SUITABLE FOR CARBUTAMIDE.|GC PROCEDURE FOR DETERMINING ANTIDIABETIC DRUGS IN THE BLOOD IS DESCRIBED. CARBUTAMIDE WAS ONE OF THE FIVE IDENTIFIED USING THIS METHOD.

Computed Properties

Molecular Weight:271.34
XLogP3:1
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:271.09906259
Monoisotopic Mass:271.09906259
Topological Polar Surface Area:110
Heavy Atom Count:18
Complexity:356
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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